JPS6234753B2 - - Google Patents
Info
- Publication number
- JPS6234753B2 JPS6234753B2 JP52145600A JP14560077A JPS6234753B2 JP S6234753 B2 JPS6234753 B2 JP S6234753B2 JP 52145600 A JP52145600 A JP 52145600A JP 14560077 A JP14560077 A JP 14560077A JP S6234753 B2 JPS6234753 B2 JP S6234753B2
- Authority
- JP
- Japan
- Prior art keywords
- aminonitrile
- reaction medium
- ketone
- mole
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 35
- 150000002576 ketones Chemical class 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 239000012429 reaction media Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 150000001299 aldehydes Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 239000012431 aqueous reaction media Substances 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 9
- -1 hydroxy, amino, carboxyl Chemical group 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 claims description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005219 aminonitrile group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Chemical class 0.000 claims description 2
- 239000000908 ammonium hydroxide Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- JQULXIOYDDCNGR-UHFFFAOYSA-N 2-amino-2-methylpropanenitrile Chemical compound CC(C)(N)C#N JQULXIOYDDCNGR-UHFFFAOYSA-N 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 description 2
- HQMLIDZJXVVKCW-UHFFFAOYSA-N 2-aminopropanamide Chemical compound CC(N)C(N)=O HQMLIDZJXVVKCW-UHFFFAOYSA-N 0.000 description 2
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- GSYTVXOARWSQSV-BYPYZUCNSA-N L-methioninamide Chemical compound CSCC[C@H](N)C(N)=O GSYTVXOARWSQSV-BYPYZUCNSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- UAMZETBJZRERCQ-UHFFFAOYSA-N alpha-aminopropionitrile Chemical compound CC(N)C#N UAMZETBJZRERCQ-UHFFFAOYSA-N 0.000 description 1
- 238000005844 autocatalytic reaction Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7636520A FR2372797A1 (fr) | 1976-12-03 | 1976-12-03 | Procede d'hydrolyse catalytique chimique d'a-amino-nitriles ou de leurs sels |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5382707A JPS5382707A (en) | 1978-07-21 |
| JPS6234753B2 true JPS6234753B2 (de) | 1987-07-28 |
Family
ID=9180640
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14559977A Granted JPS5382706A (en) | 1976-12-03 | 1977-12-02 | Process for preparing alphaaamino acid |
| JP14560077A Granted JPS5382707A (en) | 1976-12-03 | 1977-12-02 | Process for preparing alphaaaminoamid |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14559977A Granted JPS5382706A (en) | 1976-12-03 | 1977-12-02 | Process for preparing alphaaamino acid |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4243814A (de) |
| JP (2) | JPS5382706A (de) |
| BE (2) | BE861121A (de) |
| BR (1) | BR7708051A (de) |
| CA (1) | CA1104140A (de) |
| CH (2) | CH628320A5 (de) |
| CS (2) | CS223865B2 (de) |
| DD (1) | DD135486A5 (de) |
| DE (2) | DE2753828A1 (de) |
| ES (2) | ES464563A1 (de) |
| FR (1) | FR2372797A1 (de) |
| GB (1) | GB1596924A (de) |
| HU (1) | HU178411B (de) |
| IE (1) | IE45926B1 (de) |
| IT (1) | IT1093037B (de) |
| NL (2) | NL188691C (de) |
| PL (1) | PL111021B1 (de) |
| SU (2) | SU793383A3 (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4370493A (en) * | 1979-09-21 | 1983-01-25 | The United States Of America As Represented By The Secretary Of Energy | Synthesis of alpha-amino acids |
| US4375555A (en) * | 1979-09-21 | 1983-03-01 | The United States Of America As Represented By The United States Department Of Energy | Synthesis of alpha-amino acids |
| EP0067499B1 (de) * | 1981-03-26 | 1985-10-23 | Mitsubishi Gas Chemical Company, Inc. | Verfahren zur Herstellung von Alphaaminosäuren |
| FR2519973A1 (fr) * | 1982-01-15 | 1983-07-22 | Centre Nat Rech Scient | Procede d'hydrolyse catalytique d'un alpha-amino-nitrile en phase heterogene, ainsi que les resines polymeres a activite catalytique pour la mise en oeuvre du procede |
| FR2565225B1 (fr) * | 1984-06-05 | 1986-10-17 | Centre Nat Rech Scient | Procede de synthese en continu d'un a-amino-acide par hydrolyse catalytique chimique et dispositif pour la mise en oeuvre du procede |
| NL8403487A (nl) * | 1984-11-15 | 1986-06-02 | Stamicarbon | Werkwijze voor de enzymatische scheiding van dl-alfa-aminozuuramides. |
| FR2590896B1 (fr) * | 1985-12-03 | 1988-07-22 | Aec Chim Organ Biolog | Procede de preparation d'une solution aqueuse d'un sel alcalin de la methionine |
| DE4235295A1 (de) * | 1992-10-20 | 1994-04-21 | Degussa | Kontinuierlich durchführbares Verfahren zur Herstellung von Methionin oder Methioninderivaten |
| DE19518986A1 (de) * | 1995-05-29 | 1996-12-05 | Basf Ag | Verfahren zur Herstellung von Glycin-N,N-diessigsäure-Derivaten durch Umsetzung von Glycinderivaten oder deren Vorstufen mit Formaldehyd und Cyanwasserstoff oder von Iminodiacetonitril oder Imindodiessigsäure mit entsprechenden Aldehyden und Cyanwasserstoff in wäßrig-saurem Medium |
| JP2001163845A (ja) * | 1999-12-13 | 2001-06-19 | Mitsubishi Rayon Co Ltd | アミノ酸アミドの製造方法 |
| NL1015715C2 (nl) * | 2000-07-14 | 2002-01-17 | Dsm Nv | Werkwijze voor de bereiding van (schiffse basen van) alfa-alkyl-alfa-aminozuuramiden. |
| WO2004098320A1 (en) | 2003-04-16 | 2004-11-18 | Vdf Futureceuticals | Methods for coffee cherry products |
| US7815959B2 (en) | 2003-04-16 | 2010-10-19 | Vdf Futureceuticals, Inc. | Low-mycotoxin coffee cherry products |
| JP4340317B2 (ja) | 2004-04-08 | 2009-10-07 | ブイ・デイ・エフ・フユーチヤーシユーテイカルズ・インコーポレイテツド | コーヒー果粒化粧組成物及び方法 |
| FR2890966A1 (fr) * | 2005-09-21 | 2007-03-23 | Adisseo France Sas Soc Par Act | Hydrolyse ammoniacale du 2-hydroxy-4-(methylthio) butyronitrile, e ncontinu et sans isoler de produits intermediaires. |
| JP5613162B2 (ja) * | 2009-07-22 | 2014-10-22 | 株式会社日本ファインケム | ２−アミノブチルアミド無機酸塩の製造方法 |
| CN102827028A (zh) * | 2012-09-17 | 2012-12-19 | 浙江邦成化工有限公司 | 一种氰基酰胺化工艺 |
| EP3632896A1 (de) * | 2018-10-01 | 2020-04-08 | Evonik Operations GmbH | Herstellung von aminosäuren aus ihren aminonitrilen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2004523A (en) * | 1931-12-31 | 1935-06-11 | Ig Farbenindustrie Ag | Aminocarboxylic acids and salts thereof |
| GB908735A (en) * | 1959-12-30 | 1962-10-24 | Ajinomoto Kk | Process for synthesising amino acids |
| US3387031A (en) * | 1961-06-08 | 1968-06-04 | Union Carbide Corp | Synthesis of alpha-amino acid amide hydrohalides |
| DE1543832B2 (de) * | 1965-06-04 | 1977-05-18 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von alpha-aminocarbonsaeuren |
| NL6515920A (de) * | 1965-12-08 | 1967-06-09 | ||
| US3867436A (en) * | 1973-07-09 | 1975-02-18 | Ajinomoto Kk | Method of preparing phenylalanine |
| NL182954C (nl) * | 1975-08-20 | 1988-06-16 | Stamicarbon | Werkwijze voor het bereiden van alfa-aminozuuramide. |
| US4072698A (en) * | 1976-12-02 | 1978-02-07 | The Upjohn Company | Resolution of aminonitriles |
-
1976
- 1976-12-03 FR FR7636520A patent/FR2372797A1/fr active Granted
-
1977
- 1977-11-22 CH CH1423177A patent/CH628320A5/fr not_active IP Right Cessation
- 1977-11-23 BE BE182872A patent/BE861121A/xx not_active IP Right Cessation
- 1977-11-24 BE BE182913A patent/BE861172A/xx not_active IP Right Cessation
- 1977-11-28 CA CA291,839A patent/CA1104140A/fr not_active Expired
- 1977-11-29 HU HU77AA885A patent/HU178411B/hu not_active IP Right Cessation
- 1977-11-29 ES ES464563A patent/ES464563A1/es not_active Expired
- 1977-11-29 ES ES464564A patent/ES464564A1/es not_active Expired
- 1977-12-01 IT IT69713/77A patent/IT1093037B/it active
- 1977-12-01 NL NLAANVRAGE7713289,A patent/NL188691C/xx not_active IP Right Cessation
- 1977-12-01 IE IE2437/77A patent/IE45926B1/en not_active IP Right Cessation
- 1977-12-01 PL PL1977202573A patent/PL111021B1/pl not_active IP Right Cessation
- 1977-12-01 US US05/856,320 patent/US4243814A/en not_active Expired - Lifetime
- 1977-12-01 NL NLAANVRAGE7713308,A patent/NL187436C/xx not_active IP Right Cessation
- 1977-12-02 JP JP14559977A patent/JPS5382706A/ja active Granted
- 1977-12-02 CS CS778045A patent/CS223865B2/cs unknown
- 1977-12-02 CS CS794936A patent/CS223880B2/cs unknown
- 1977-12-02 JP JP14560077A patent/JPS5382707A/ja active Granted
- 1977-12-02 DD DD77202378A patent/DD135486A5/de unknown
- 1977-12-02 DE DE19772753828 patent/DE2753828A1/de active Granted
- 1977-12-02 GB GB50303/77A patent/GB1596924A/en not_active Expired
- 1977-12-02 SU SU772548904A patent/SU793383A3/ru active
- 1977-12-02 DE DE19772753829 patent/DE2753829A1/de active Granted
- 1977-12-02 BR BR7708051A patent/BR7708051A/pt unknown
-
1979
- 1979-08-03 SU SU792799652A patent/SU1220568A3/ru active
-
1981
- 1981-03-06 CH CH156681A patent/CH629473A5/fr not_active IP Right Cessation
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